Hydrochloric Acid → 8,8,9,9,9-Pentafluorononan-1-ol

HRID 1837215Notes

Reaction equation

HRID 1837215 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([F:22])([F:21])[C:17]([F:20])([F:19])[F:18])C1C=CC=CC=1.CN(C)C1C=CC=CC=1.[Cl-].[Cl-].[Cl-].[Al+3].Cl>C(Cl)Cl>[F:21][C:16]([F:22])([C:17]([F:18])([F:19])[F:20])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][OH:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 949N,N-DimethylanilineHCID 6451240Aluminum(III) ChlorideHCID 234971211-Benzyloxy-8,8,9,9,9-pentafluorononane

Product 1

HCID 113682968,8,9,9,9-Pentafluorononan-1-olYield 74.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

16 g of 1-benzyloxy-8,8,9,9,9-pentafluoro-nonane is dissolved in 700 ml of absolute methylene chloride, mixed with 18.4 ml of N,N-dimethylaniline at 0° C. and stirred for 5 minutes. Then, 26.4 g of aluminum trichloride is added in portions, and the reaction mixture is heated for 45 minutes to 50° C. For working-up, the batch is allowed to come to room temperature, it is stirred into 2N hydrochloric acid, extracted 3 times with methylene chloride, dried on magnesium sulfate and concentrated by evaporation in a vacuum. The crude product is chromatographed on silica gel with a hexane-ethyl acetate gradient. 8.6 g of 8,8,9,9,9-pentafluoro-nonan-1-ol is obtained as an oil.

Workup

  1. temperaturethe reaction mixture is heated for 45 minutes to 50° C
  2. customto come to room temperature
  3. extractionextracted 3 times with methylene chloride
  4. customdried on magnesium sulfate
  5. concentrationconcentrated by evaporation in a vacuum
  6. customThe crude product is chromatographed on silica gel with a hexane-ethyl acetate gradient

Sources & evidence

ORD record
ord-a375287c63fe4a74bf5697200063c0d6
Source dataset
uspto-grants-2004_08
Patent number
US06780855B2

Reaction notes

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